I've been playing PES for 7 years now, and for every new version that comes out, I just go into free training and mess around, explore for at least half an hour. Get a hold of the controls, see what can be done, etc. Then I play a few simple matches with difficulty set low, try things out. It seems to work.
As for your dribbling question, you can either drag the player along with the cursor (you can make him run or sprint) or you can use the nunchuk joystick to just make him dribble at a normal speed. If you drag with cursor, you can also press left or right on the joystick to make him sidestep left or right, and pressing forwards will make him dribble with long steps, while pressing down will make him stop for a second. Just explore the controls a bit in training.
Also, you guys, go
here and share your friend codes! The online for PES2008 is great fun!